JP2001019683A - Derivative of 1,2-benzisothiazolin-3-one and its preparation - Google Patents
Derivative of 1,2-benzisothiazolin-3-one and its preparationInfo
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- JP2001019683A JP2001019683A JP11195491A JP19549199A JP2001019683A JP 2001019683 A JP2001019683 A JP 2001019683A JP 11195491 A JP11195491 A JP 11195491A JP 19549199 A JP19549199 A JP 19549199A JP 2001019683 A JP2001019683 A JP 2001019683A
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- JP
- Japan
- Prior art keywords
- benzisothiazolin
- compound
- derivative
- reaction
- substituent
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- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- Thiazole And Isothizaole Compounds (AREA)
Abstract
Description
【0001】[0001]
【発明の属する技術分野】本発明は,1,2-ベンゾイソチ
アゾリン-3-オン化合物誘導体の製造方法に関するもの
である。さらに詳しくは,1,2-ベンゾイソチアゾリン-3
-オン化合物誘導体をスルフェンアミド化合物を加熱す
ることにより,効率よく製造する方法に関するものであ
る。The present invention relates to a method for producing a 1,2-benzisothiazolin-3-one compound derivative. More specifically, 1,2-benzisothiazoline-3
The present invention relates to a method for efficiently producing a -one compound derivative by heating a sulfenamide compound.
【0002】[0002]
【従来の技術】1,2-ベンゾイソチアゾリン-3-オン化合
物誘導体は種々の生理活性を持つ事が知られており,た
とえば5-クロロおよび6-クロロ-1,2-ベンゾイソチアゾ
リン-3-オンは抗菌・抗バクテリア活性があることが報
告されている(Adv. Heterocycl.Chem., 14, 58 (197
2))。さらに,1,2-ベンゾイソチアゾリン-3-オンから
誘導されるさまざまな1,2-ベンゾイソチアゾール化合物
のうち,イソチアゾール環部分に置換基を有する化合物
も,種々の薬理作用を示す化合物が存在することが報告
されているという重要な化合物である(Adv. Heterocyc
l. Chem., 14, 58 (1972),J. Med. Chem., 29, 359 (1
986))。特に,2位の窒素原子上に置換基を有する1,2-
ベンゾイソチアゾリン-3-オン化合物誘導体は,抗菌・
抗バクテリア作用を示す化合物があることが報告されて
いる(Bull. Chem. Soc. Jpn., 55, 1183 (1982))。ま
た,1,2-ベンゾイソチアゾリン-3-オンを酸化すること
により甘味料であるサッカリンを得ることもできる(J.
Chem. Soc., 123, 170 (1923),Chem. Ber., 61, 1308
(1928))。2. Description of the Related Art 1,2-Benzoisothiazolin-3-one compound derivatives are known to have various physiological activities, for example, 5-chloro and 6-chloro-1,2-benzoisothiazolin-3-one. Has been reported to have antibacterial and antibacterial activities (Adv. Heterocycl. Chem., 14, 58 (197
2)). Furthermore, among the various 1,2-benzisothiazole compounds derived from 1,2-benzisothiazolin-3-one, there are compounds having a substituent at the isothiazole ring part, as well as compounds exhibiting various pharmacological actions. Is an important compound that has been reported to work (Adv. Heterocyc
l. Chem., 14, 58 (1972), J. Med. Chem., 29, 359 (1
986)). In particular, 1,2-having a substituent on the nitrogen atom at the 2-position
Benzoisothiazolin-3-one compound derivatives are
It has been reported that some compounds exhibit antibacterial activity (Bull. Chem. Soc. Jpn., 55, 1183 (1982)). Saccharin, a sweetener, can also be obtained by oxidizing 1,2-benzisothiazolin-3-one (J.
Chem. Soc., 123, 170 (1923), Chem. Ber., 61, 1308.
(1928)).
【0003】従来,1,2-ベンゾイソチアゾリン-3-オン
化合物誘導体は,ジチオサリチル酸やチオサリチル酸を
塩素あるいは臭素と処理をした後,アミンと反応させる
方法(米国特許第2870015号,ベルギー国特許第565380
号,第617384号,ドイツ国特許第1135468号,J. Org. C
hem.,40, 2029 (1975)),あるいはチオサリチル酸アミ
ド類と塩素を反応させる方法(Farmaco, Ed. Sci., 16,
509 (1961), 18, 732(1963), 19, 254 (1964), 22, 93
5, 989, 999 (1967), 23, 468 (1968), 英国特許第8481
30号,米国特許第3761489号)により製造されていた
が,有毒な塩素や臭素を用いなければならず,また製造
装置の腐食の問題もあるので,安全な製造法の開発が望
まれている。また,1,2-ベンゾジチオール-3-オンや1,2
-ベンゾジチオール-3-オン 1-オキシドより製造する方
法も知られているが(J. Chem.Soc., 123, 170 (1923),
Tetrahedron Lett., 37, 5337 (1996)),これらの化
合物はいずれも特殊な試薬であって,入手が容易ではな
く工業的に実施する方法としては不適当である。Conventionally, 1,2-benzisothiazolin-3-one compound derivatives have been prepared by treating dithiosalicylic acid or thiosalicylic acid with chlorine or bromine and then reacting with amines (US Pat. No. 2870015, Belgian Patent 565380
No. 617384, German Patent No. 1135468, J. Org. C
hem., 40, 2029 (1975)) or a method of reacting thiosalicylic amides with chlorine (Farmaco, Ed. Sci., 16,
509 (1961), 18, 732 (1963), 19, 254 (1964), 22, 93
5, 989, 999 (1967), 23, 468 (1968), UK Patent No. 8481
No. 30, U.S. Pat. No. 3,761,489), but the development of a safe manufacturing method is desired because toxic chlorine and bromine must be used, and there is a problem of corrosion of the manufacturing equipment. . In addition, 1,2-benzodithiol-3-one and 1,2
There is also known a method for producing from -benzodithiol-3-one 1-oxide (J. Chem. Soc., 123, 170 (1923),
Tetrahedron Lett., 37, 5337 (1996)), these compounds are all special reagents, are not readily available, and are unsuitable for industrial practice.
【0004】[0004]
【発明が解決しようとする課題】本発明は,1,2-ベンゾ
イソチアゾリン-3-オン化合物誘導体を製造するにあた
り,通常の方法である有毒な塩素ガスを用いるという欠
点を克服し,1,2-ベンゾイソチアゾリン-3-オン化合物
誘導体を製造するための工業的に有利な方法を提供する
ことを目的としてなされたものである。DISCLOSURE OF THE INVENTION The present invention overcomes the drawback of using a toxic chlorine gas, which is a conventional method, in producing a 1,2-benzisothiazolin-3-one compound derivative. The purpose of the present invention is to provide an industrially advantageous method for producing a -benzoisothiazolin-3-one compound derivative.
【0005】[0005]
【課題を解決するための手段】本発明者らは,1,2-ベン
ゾイソチアゾリン-3-オン化合物誘導体の製造方法につ
いて鋭意研究を重ねた結果,スルフェンアミド化合物を
加熱することにより環化反応を起こさせれば,安全かつ
容易に1,2-ベンゾイソチアゾリン-3-オン化合物誘導体
が得られることを見い出し,この知見に基づいて本発明
を完成するに至った。Means for Solving the Problems The present inventors have conducted intensive studies on a method for producing a 1,2-benzisothiazolin-3-one compound derivative, and as a result, have found that a cyclization reaction can be achieved by heating a sulfenamide compound. The present inventors have found that a 1,2-benzisothiazolin-3-one compound derivative can be obtained safely and easily by causing the above, and based on this finding, the present invention has been completed.
【0006】すなわち,本発明によれば,下記一般式
(イ)That is, according to the present invention, the following general formula (A)
【化3】 (式中,R1〜R4は水素または置換基を示し,R5は
置換基を示す)で表される1,2-ベンゾイソチアゾリン-3
-オン化合物誘導体を製造する方法において,下記一般
式(ロ)Embedded image (Wherein, R 1 to R 4 represent hydrogen or a substituent, and R 5 represents a substituent).
In the method for producing a -one compound derivative, the following general formula (II)
【化4】 (式中,R1〜R4は水素または置換基を示し,R5は
置換基を示す)で表されるスルフェンアミド化合物を環
化反応をさせることを特徴とする1,2-ベンゾイソチアゾ
リン-3-オン化合物誘導体の製造方法が提供される。Embedded image Wherein R 1 to R 4 represent hydrogen or a substituent, and R 5 represents a substituent, wherein the sulfenamide compound represented by the formula ( 1 ) is subjected to a cyclization reaction. A method for producing a 3-one compound derivative is provided.
【0007】[0007]
【発明実施の形態】本発明の製造目的化合物である1,2-
ベンゾイソチアゾリン-3-オン化合物誘導体を示す前記
一般式(イ)において,R1〜R4は水素または置換基
を示すが,この場合の置換基は,本発明の反応に不活性
なものであればどのようなものでもよい。このような置
換基には,鎖状または環状のアルキル基,アルコキシ
基,ジアルキルアミノ基,アシル基,アルコキシカルボ
ニル基,ハロゲン原子,シアノ基,ニトロ基等が包含さ
れる。これらの置換基に結合するアルキル基の炭素数
は,通常1〜6である。また,R5は有機基を示すが,
この場合の有機基にはアルキル基やシクロアルキル基で
ある脂肪族基が包含される。アルキル基の炭素数は1〜
12,好ましくは1〜6である。これらのアルキル基お
よびシクロアルキル基は,ハロゲン原子,アルコキシル
基,ジアルキルアミノ基,アシル基,アルコキシカルボ
ニル基等の置換基を有していてもよい。これらの置換基
におけるアルキル基は,炭素数1〜6の低級アルキル基
であることができる。前記脂肪族基の具体例を示すと、
メチル、エチル、プロピル、イソプロピル、ブチル、ヘ
キシル、シクロヘキシル、メトキシ、エトキシ、ジメチ
ルアミノ、ジエチルアミノ、アセチル、メトキシカルボ
ニル、エトキシカルボニル、クロロ、ブロモ等が挙げら
れる。BEST MODE FOR CARRYING OUT THE INVENTION 1,2-
In the above general formula (A), which represents a benzoisothiazolin-3-one compound derivative, R 1 to R 4 represent hydrogen or a substituent. In this case, the substituent may be one which is inert to the reaction of the present invention. Anything may be used. Such substituents include a chain or cyclic alkyl group, alkoxy group, dialkylamino group, acyl group, alkoxycarbonyl group, halogen atom, cyano group, nitro group and the like. The alkyl group bonded to these substituents usually has 1 to 6 carbon atoms. R 5 represents an organic group,
The organic group in this case includes an aliphatic group such as an alkyl group or a cycloalkyl group. The carbon number of the alkyl group is 1 to
12, preferably 1 to 6. These alkyl groups and cycloalkyl groups may have a substituent such as a halogen atom, an alkoxyl group, a dialkylamino group, an acyl group, or an alkoxycarbonyl group. The alkyl group in these substituents can be a lower alkyl group having 1 to 6 carbon atoms. To show a specific example of the aliphatic group,
Methyl, ethyl, propyl, isopropyl, butyl, hexyl, cyclohexyl, methoxy, ethoxy, dimethylamino, diethylamino, acetyl, methoxycarbonyl, ethoxycarbonyl, chloro, bromo and the like.
【0008】1,2-ベンゾイソチアゾリン-3-オン類の製
造は,好ましくは反応溶媒の存在下で実施されるが,こ
の場合の反応溶媒は,ベンゼン,トルエン,キシレン,
クロロベンゼン,ジクロロベンゼン,アニソール等の無
極性有機溶媒中で行われる。また,これらの溶媒は単独
または混合溶媒の形で使用される。The production of 1,2-benzisothiazolin-3-ones is preferably carried out in the presence of a reaction solvent, wherein the reaction solvent is benzene, toluene, xylene,
The reaction is performed in a non-polar organic solvent such as chlorobenzene, dichlorobenzene, and anisole. These solvents are used alone or in the form of a mixed solvent.
【0009】前記製造方法における温度は50度〜15
0度付近の温度で行うことができるが,あまり低温すぎ
ると反応時間が遅くなり,高すぎると分解反応や副反応
が多くなるので,80度〜120度の範囲で実施するの
が好ましい。反応時間は反応温度により左右され,一概
に定めることはできないが,通常は2〜8時間で十分で
ある。[0009] The temperature in the above-mentioned manufacturing method is 50 to 15 degrees.
The reaction can be carried out at a temperature around 0 ° C. However, if the temperature is too low, the reaction time will be delayed, and if it is too high, the decomposition reaction and side reactions will increase. The reaction time depends on the reaction temperature and cannot be determined unconditionally, but usually 2 to 8 hours is sufficient.
【0010】このようにして,本発明の反応によって例
えば化学式(1)〜(2)で示される1,2-ベンゾイソチ
アゾリン-3-オン化合物誘導体を製造することができ
る。Thus, the 1,2-benzisothiazolin-3-one compound derivative represented by, for example, chemical formulas (1) and (2) can be produced by the reaction of the present invention.
【化5】 Embedded image
【0011】[0011]
【実施例】次に,本発明を実施例により詳細に説明す
る。なお,本発明の実施例は本発明の理解を容易にする
ために代表的な物をあげたものであり,本発明はこれだ
けに限定されるものではない。なお,下記実施例によっ
て製造される1,2-ベンゾイソチアゾリン-3-オン化合物
誘導体は,すべて新規化合物であり,各種スペクトルと
元素分析の結果を主要な判定基準として同定した。ま
た,製造された化合物(1)〜(2)は,前記で示した
化合物(1)〜(2)に対応するもので,その物性値と
しては,融点,核磁気共鳴スペクトル(1H−NM
R),赤外吸収スペクトル(IR),元素分析値の順に
それぞれ記した。Next, the present invention will be described in detail with reference to examples. It should be noted that the embodiments of the present invention are representative ones for easy understanding of the present invention, and the present invention is not limited to these. The 1,2-benzisothiazolin-3-one compound derivatives produced in the following examples are all novel compounds, and the results of various spectra and elemental analysis were identified as main criteria. Moreover, the prepared compound (1) to (2), which corresponds to the compound described in above (1) to (2), as the values of the physical properties, melting point, nuclear magnetic resonance spectra (1 H-NM
R), infrared absorption spectrum (IR), and elemental analysis values.
【0012】実施例1 内容積50mlのガラス製容器中に2-スルフェナモイル
安息香酸メチル(2mmol)をトルエン(10ml)
に溶解させ,100℃で5時間攪拌した。トルエンを減
圧下留去させ,粗生成物をシリカゲルクロマトグラフィ
ー(溶出溶媒塩化メチレン:アセトン:メタノール=1
00:5:1)で精製した。さらにベンゼン−ヘキサン
で再結晶することにより前記化合物(1)の1,2-ベンゾ
イソチアゾリン-3-オンを得た。 収率 58%;融点 187.5-189 ℃;1H-NMR(CDCl3) 3.
98 (3H, s), 6.83 (1H, dt, J=8, 1 Hz), 7.24 (1H, d
d, J=7, 1 Hz), 7.40-7.47 (2H, m), 7.57 (1H,d, J=8
Hz), 7.71 (1H, td, J=8, 1 Hz), 8.06 (1H, dd, J=8,
1 Hz), 8.13 (1H, d, J=8 Hz);IR(KBr) 1688, 1318, 1
281, 1107, 733 cm−1。 C15H11NO3Sとしての元素分析値(%) 測定値:C, 56.69, H, 3.42, N, 4.36 計算値:C, 56.76, H, 3.49, N, 4.41EXAMPLE 1 Methyl 2-sulfenamoyl benzoate (2 mmol) was placed in a glass container having an internal volume of 50 ml and toluene (10 ml).
And stirred at 100 ° C. for 5 hours. The toluene was distilled off under reduced pressure, and the crude product was subjected to silica gel chromatography (elution solvent: methylene chloride: acetone: methanol = 1).
00: 5: 1). Further, recrystallization from benzene-hexane gave 1,2-benzoisothiazolin-3-one of the compound (1). Yield 58%; melting point 187.5-189 ° C; 1 H-NMR (CDCl 3 ) 3.
98 (3H, s), 6.83 (1H, dt, J = 8, 1 Hz), 7.24 (1H, d
d, J = 7, 1 Hz), 7.40-7.47 (2H, m), 7.57 (1H, d, J = 8
Hz), 7.71 (1H, td, J = 8, 1 Hz), 8.06 (1H, dd, J = 8,
1 Hz), 8.13 (1H, d, J = 8 Hz); IR (KBr) 1688, 1318, 1
281, 1107, 733 cm -1 . Elemental analysis value (%) as C 15 H 11 NO 3 S Measurement value: C, 56.69, H, 3.42, N, 4.36 Calculated value: C, 56.76, H, 3.49, N, 4.41
【0013】実施例2 実施例1において,2-スルフェナモイル安息香酸メチル
の代わりに5-クロロ-2-スルフェナモイル安息香酸メチ
ルを用いて,前記化合物(2)の1,2-ベンゾイソチアゾ
リン-3-オンを得た。 収率 29%;融点 193-194 ℃;1H-NMR(CDCl3) 3.99
(3H, s), 6.72 (1H,dd, J=9, 1 Hz), 7.39 (1H, dt, J
=9, 2 Hz), 7.52 (1H, dd, J=9, 1 Hz), 7.66-7.69 (1
H, m), 8.04 (1H, t, J=2 Hz), 8.10 (1H, t, J=2 H
z);IR(KBr) 1703,1669, 1449, 1308, 1252, 1123 cm
−1。 C15H9Cl2NO3S2としての元素分析値(%) 測定値:C, 46.95, H, 2.31, N, 3.50 計算値:C, 46.64, H, 2.35, N, 3.63Example 2 The procedure of Example 1 was repeated, except that methyl 5-chloro-2-sulfenamoylbenzoate was used in place of methyl 2-sulfenamoylbenzoate. I got Yield 29%; Melting point 193-194 ° C; 1 H-NMR (CDCl 3 ) 3.99
(3H, s), 6.72 (1H, dd, J = 9, 1 Hz), 7.39 (1H, dt, J
= 9, 2 Hz), 7.52 (1H, dd, J = 9, 1 Hz), 7.66-7.69 (1
H, m), 8.04 (1H, t, J = 2 Hz), 8.10 (1H, t, J = 2 H
z); IR (KBr) 1703,1669, 1449, 1308, 1252, 1123 cm
-1 . C 15 H 9 Cl 2 NO 3 Elementary analysis as S 2 (%) measurements: C, 46.95, H, 2.31 , N, 3.50 Calculated: C, 46.64, H, 2.35 , N, 3.63
【0014】[0014]
【発明の効果】本発明におけるスルフェンアミド化合物
の反応により,1,2-ベンゾイソチアゾリン-3-オン化合
物誘導体を収率よく製造することができる。しかも,有
毒なガスを用いることなく安全に製造できるので,工業
的な1,2-ベンゾイソチアゾリン-3-オン化合物誘導体の
合成法として最適である。According to the present invention, a 1,2-benzisothiazolin-3-one compound derivative can be produced in good yield by the reaction of the sulfenamide compound in the present invention. Moreover, since it can be produced safely without using toxic gas, it is optimal as an industrial method for synthesizing 1,2-benzisothiazolin-3-one compound derivatives.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 蒲 康夫 茨城県つくば市東1ー1 物質工学工業技 術研究所内 (72)発明者 芝上 基成 茨城県つくば市東1ー1 物質工学工業技 術研究所内 (72)発明者 高木 俊之 茨城県つくば市東1ー1 物質工学工業技 術研究所内 Fターム(参考) 4C033 AA01 AA19 ──────────────────────────────────────────────────の Continuing from the front page (72) Inventor Yasuo Kama 1-1 Materials Engineering Technology Research Institute, Higashi 1-1, Tsukuba City, Ibaraki Prefecture (72) Inventor Motonori Shibagami 1-1 Materials Research Institute, Higashi 1-1 Tsukuba City, Ibaraki Prefecture (72) Inventor Toshiyuki Takagi 1-1, Higashi 1-1, Tsukuba-shi, Ibaraki F-term in the Materials Technology Institute (reference) 4C033 AA01 AA19
Claims (1)
置換基を示す)で表される1,2-ベンゾイソチアゾリン-3
-オン化合物誘導体を製造する方法において,下記一般
式(ロ) 【化2】 (式中,R1〜R4は水素または置換基を示し,R5は
置換基を示す)で表されるスルフェンアミド化合物を環
化反応をさせることを特徴とする1,2-ベンゾイソチアゾ
リン-3-オン化合物誘導体の製造方法。1. A compound represented by the following general formula (a): (Wherein, R 1 to R 4 represent hydrogen or a substituent, and R 5 represents a substituent).
In a method for producing a -one compound derivative, a compound represented by the following general formula (II): Wherein R 1 to R 4 represent hydrogen or a substituent, and R 5 represents a substituent, wherein the sulfenamide compound represented by the formula ( 1 ) is subjected to a cyclization reaction. A method for producing a 3-one compound derivative.
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2010168316A (en) * | 2009-01-23 | 2010-08-05 | National Institute Of Advanced Industrial Science & Technology | New sulfenamide compound and method for producing the same |
-
1999
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Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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JP2010168316A (en) * | 2009-01-23 | 2010-08-05 | National Institute Of Advanced Industrial Science & Technology | New sulfenamide compound and method for producing the same |
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